Originally Posted by everycredit
Make sure when you put your helmet on that your ears lay flat. Pinching your ears can cause trauma and would cause swelling.
The suggestions of a balaclava from other members is highly warranted. My helmet would hurt one or both of my ears (I have "detached" ear lobes, which has my ears sticking out more than the average person (the bottom part of the ear lobe is not attached to the face)). After getting a silk balaclava, the helmet glides on my head and my ears feel fine.
The balaclava doesn't have to be silk. Nylon or even cotton would probably work well (although cotton would wear down quickly, I would think).
Ice and Advil helps for swelling in your ear.
I have the same ear pain issues with a new helmet. I found wearing a head wrap that covers my ears solved the problem.